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In 1961 Wieboldt's enlarged itself by acquiring the failed Mandel Brothers store on State St as well as a smaller branch store in Lincoln Village shopping center. Prior to that time there were five Chicago neighborhood stores; Grand and Ashland, Milwaukee and Paulina, Lincoln and Belmont, Halsted and 63rd St., and Ashland and Monroe.They also had several suburban stores including locations in Evanston, Lombard, Norridge, and Oak Park IL.[1] By the 1970s Wieboldt's operated over 15 stores in the Chicago area.[citation needed]

Wieboldt's was known for their good values, unpretentious merchandise, and multilingual sales staff, the stores were especially popular among ethnic, working-class shoppers who could not afford or did not like to shop at the big downtown department stores. Wieboldt's former slogan was "Where You Buy With Confidence!".

They celebrated 100 years in business in April 1983. An advertisement in the Chicago Sun-Times stated "Building for a New Tomorrow". "An important part of Chicago's past, we look to the future with confidence and enthusiasm. The dream of yesterday is the promise of tomorrow. Chicago, Wieboldt's. Tomorrow begins today."[2]

During the 1980s the chain had trouble staying profitable, eventually leading the company into bankruptcy in 1987. The chain never recovered and all the stores closed.

Wieboldt's was known for giving S&H Green Stamps with purchases and had redemption centers located in their stores. The State St. location included a large redemption center. Customers would choose items based on the number of stamps turned in for redemption. In the 1940s and 1950s they sponsored a radio program featuring The Cinnamon Bear. Later they had a television program called The Cinnamon Bear. The shows were stories of how Cinnamon Bear takes his young friends on a trip to maybe land in search of the silver star. A stuffed teddy bear version could be purchased from the stores for $2.98 in the 1950s. Santa would give out free Cinnamon Bear buttons to children visiting Santa. The program was first produced by Glen Heisch and Elizabeth Heisch in 1937 in Hollywood and syndicated around the country.[3]